Is it possible to read a fascinating true story about a professional roulette player where gambling is not placed on a pedestal nor glamorized? I believe the answer is yes if you listen to or read The Gambler’s Game by James Darnborough, the grandson of a legendary professional gambler known for breaking the bank at Monte Carlo at the turn of the 20th century. This is a five-star biography.
Interview Highlights
- The definition of a rebound book.
- Mark’s comparison of James to Laura Hillenbrand and why.
- Mark’s book pairings of Fortune’s Formula and Gambler: Secrets from a Life at Risk by Billy Walters.
- The big baseball question: What happens if Bill becomes an elite baseball player while making it to the majors? Does he still make it to Monte Carlo?
- Spotting an easy mark in the 1890s and why it didn’t happen more often to Bill.
- The reason Bill chose poker over roulette (this response from James is critical to better grasp and appreciate Bill’s goals and objectives as a professional gambler).
- Professional gambling vs. addictive or compulsive gambling. Bill was the former.
- The reason others tried to crack Bill’s code of success and why they couldn’t and didn’t.
- The main reason Bill failed to run a casino. Does this mean the advice of Charlie Munger on circles of competence is accurate, especially in Bill’s case?
- The second act in this book is what Mark calls The Education of a Professional Gambler, a storyline that includes failure, new insights, and finding success in a repeatable system.
- I learned a new term: biased roulette wheels.
- The wealth Bill had accumulated before he traveled to Monte Carlo.
- “You have to expect to lose and still be okay (in the end).”
- The reasons Bill never experienced being robbed as fame and fortune came his way.
- In short, Bill’s advice on gambling was, “Don’t do what I do.”
- Does the book have the HEA ending? And what happened next, according to James?
In the twilight of the 19th century, as the Old West collides with the opulence of the Gilded Age, one man embarks on a journey that will redefine his life. The Gambler's Game is a captivating historical fiction saga that follows the extraordinary life of the Illinois-born baseball player turned high-stakes gambler. His audacious spirit leads him from the dust-choked plains of Nebraska to the refined ambiance of English garden parties and the allure of Belle Époque Monte Carlo.
Mark’s Favorite Lines in The Gambler’s Game
Regarding a typical day at the roulette table:
After eight hours, he has hardly changed his betting sequence and always waits until the last possible moment to place his bets.
On the way others described him as a professional gambler:
He is possibly the most dedicated player I have seen in all my years of service, and he only takes breaks to use the facilities, and occasionally he eats some food.” “I hear he declines party invitations.
Ledger of winnings and losses:
Here, roughly, are his figures for a few days: Monday, won $20,000; Tuesday, won $38,000; Wednesday, lost $30,000; Thursday, won $30,000. He takes losses and winnings alike with admirable equanimity, and while the onlooking throng emits involuntary gasps of excitement when the ball settles, Darnborough looks unconcerned.
One evening, Bill is up 14,400 FF and wins a further 22,800 FF on number 31. He loses nearly everything over the next hour but claws his way back with some clever hedging strategies. He looks relaxed and in control, but inside, he is tense with the anticipation of every spin. In all his years, he has never had such a good run in one sitting.
Bill’s advice on gambling:
You do understand that roulette is a game of chance, sir? Contrary to what you may have read about me in the papers, I do not have an infallible system, and there is no nefarious, covert mechanism by which I can guarantee to win. I do not bribe any of the casino officials, and there are no biased wheels left in Monte Carlo, as they check them meticulously every morning.
The reality of gambling is that 99 out of 100 people end up returning to the tables again and again until there is nothing left. In my experience, the people I have witnessed continue to play on out of sheer greed, even if they’re on a winning streak. Those who have lost nearly everything borrow more money and sink further into the abyss. I don’t mind telling you that I have quite an impressive collection of diamonds to prove it.
Everything I have done is a means to an end. When I play roulette, I play for hours at a time, nearly always on my feet. I am not a big socializer and have no interest in the gossip of the town. If I had chosen a different path, say an insurance agent or an accountant, then I would be working in a dreary office somewhere and not have the opportunity to be sitting at the top of a castle in
Book Club Questions
After I finished the audio version and started reading the text, a part of me wished I could run ideas by others also reading the book.
Should you add this title to your book club, here are a few questions to consider:
- Mark calls this a highly philosophical book. Why, and do you concur?
- Does Bill still go to Monte Carlo if he achieves success in baseball?
- Bill was not a compulsive gambler. What does that mean?
- Had you decided to become a professional gambler, would you have chosen poker or roulette, and why?
- He declined the expense of wine in favor of water. After standing for eight hours at the table, he hardly changed his sequence of betting. How did pitching in the minor leagues prepare him for his new career?
- Bill has several strong lines in the book about why someone should not gamble the way he did. Find and reread those lines. What would you add to his comments?
- “How much is enough?” Why did Bill ask that question in the last third of the book during the Monte Carlo era?
- Regarding the story The Rich Boy, how was Bill different from Fitzgerald’s fictional character?
Books Mentioned During the Interview
Your Next Listen
If you liked this show, I highly recommend the conversation with Mark Paul and what he calls “the greatest gambling story ever told.”

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